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Boron Carboxylate Catalysis of Homoallylboration

Gabrielle J. Dugas, Yu-hong Lam, K. N. Houk* and Isaac J. Krauss*

*University of California, Los Angeles, California 90095-1569, United States; Brandeis University, Waltham, Massachusetts 02454-9110, United States, Email: houkchem.ucla.edu, kraussibrandeis.edu

G. J. Dugas, Y.-h. Lam, K. N. Houk, I. J. Krauss, J. Org. Chem., 2014, 79, 4277-4278.

DOI: 10.1021/jo500599h (free Supporting Information)


Abstract

Boron tris(trifluoroacetate) is an effective catalyst for the homoallyl- and homocrotylboration of aldehydes by cyclopropylcarbinylboronates. This work shows that carboxylates are viable catalytic ligands for homoallyl- and homocrotylations of carbonyl compounds and opens the door to the development of catalytic asymmetric versions of this transformation.

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Key Words

1,2-addition


ID: J42-Y2014